Anionic N-fries rearrangement of N-carbamoyl diarylamines to anthranilamides. Methodology and application to acridone and pyranoacridone alkaloids.

[reaction: see text] A general alkyllithium/LDA-mediated rearrangement of N-carbamoyl diarylamines 7a-g into the anthranilamides 8a-g and 9a-g (Table 1) is presented and applied to a regioselective efficient construction of acridone (17) and pyranoacridone (18) alkaloids (Scheme 4).